Money Integrity

What Selling A Bad Deal Taught Me About Myself

I poured over my new clients paperwork, hoping to find something different but increasingly realizing it was hopeless. 

They were sold a bad deal. 

Not by me. Almost a year earlier, a salesperson who was long gone, had transitioned my client to a new product and it seems like the sales person forgot to mention to the company that they were on a premium plan that they did not need. 

Now this company was my client, their renewal was coming up, and churn was in my future if I didn’t get them to resign the same bad deal. 

On the calls leading up to the renewal, I asked a thousand questions to see if I was wrong. 

Did they ever use the extra security?

No. 

Did they have a purpose for the fancy extra tools that were included?

No. 

Amazing.

The company was happy with the product and wanted to renew at a flat rate. They weren’t being scammed, they didn’t know a cheaper option existed that seemed to better fit their needs. A few tens of thousands of dollars cheaper. 

It wasn’t a deal I would’ve sold them. I’m not blaming the sales person before me, I see how this happened, but that person was long gone and the hot potato was in my hands. 

What made things worse was I was a few months into a new job and realized that they had a pretty wild policy for deals that churned. 

If the client renewed their contract for any less money than the initial deal, that is considered churn. 

At my old sales company, if you were expected to bring in a deal and it didn’t come in, you had to make up for the money by selling or upselling another company so that you could hit your quota.  

At this new company, I was not only responsible for hitting my quota, I also had to give the money back to the organization that had been paid out in “my” bonus from the year before. Money I had never received because I wasn’t the sales person who had originally closed this deal. 

So I was stressed. 

The day of my renewal call with my client, everything seemed to go wrong. 

I made it clear to my manager that I needed her on the call because I was worried the client would ask about the premium product they were renewing. They may even just say, “Oh, there’s a cheaper option? Let’s do that.” 

My manager was a killer sales woman and I knew having her in my corner would help me combat any objections. 

At the least, if everything blew up, she’d see that it wasn’t my fault. 

I hopped on a zoom call with my client and waited a minute for my manager. 

She wasn’t there.

She was notorious for showing up late to everything, so I started the presentation without her. 

Ten minutes. 

Twenty minutes. 

As time inched forward, I started to get worried. I dragged through the details of every slide deck I made. I could see the CTO was getting impatient, but he was kind enough not to rush me. 

40 minutes into the meeting, my manager finally showed up. 

We finished the call, got the green light from the client to send over the new contract. I even pulled in a few extra dollars because I scaled back their discount. 

I don’t remember if my manager apologized for showing up late, but instead of providing criticism at the end, she simply let me know that I did a good job. 

I did do a good job. Through some clever positioning, I convinced the company to resign and even increase their spending. 

Yet, I felt terrible. 

In my whole sales career, I had never felt like I had sold a deal out of integrity until that moment. 

Sure, I always try to get the most out of every deal, but in a proper sales role, you’re trained to qualify a potential client and sell them something that solves their problems. 

My success in sales came from building great long term relationships. I was strict on discounts (as in, no discounts) because I believed in the quality of the products that I sold to my clients. If I thought they didn’t need something, I would tell them that. 

My relationships were so good that at my last company, there were multiple times my managers would assign me clients that had issues with their sales representative and asked me to help smooth things over.

This deal felt different. Even though I got the outcome I wanted, I didn’t feel great about it. I didn’t even show my client the cheaper option because I was so afraid they’d say they’d prefer to go with that one.

That deal taught me a lot about who I wanted to be. 

When I was reflecting on how I felt, I realized that I acted out from a place of fear. 

I wasn’t only nervous because I didn’t want to pay the money back. Looking back, I’m sure I could’ve argued that the situation was unfair. Even if I was punished for it, I would have at least felt as though I did the right thing. 

After closing that deal, I promised I wouldn’t compromise my integrity for a deal again. Even if that hurt me. 

Of course, no promise to the universe is complete without a test. 

A few months later, another client of mine was struggling. 

Our relationship had started out poorly. They were given to me the same way the other was, with a lot of promise that they’d one day be a huge client. 

Instead they ambushed me early on and demanded I bring our CEO into a conversation with them so that they could add more money onto their contract. 

I looked over the contract at saw that they were oversold, but based on the ambush, I could see how the previous salesperson saw their eagerness and signed them up for the biggest deal possible. 

I had to tell them no, I would not bring our busy CEO onto the call and would also not consider upselling them until they started using all the products. 

A few months later, the COVID shutdowns wrecked their business. They sold retail software and a few of their biggest clients went bankrupt. 

Their team was stubborn at first and didn’t want to admit their struggling business meant they had overpaid for their contract. 

After talking in circles with them over a few different meetings, I finally sat them down, went through every number and projection with them and forced them to acknowledge that they were going to lose hundreds of thousands of dollars with our current deal. 

They asked me if I could help, and I promised to go to bat for them. 

My old manager had been let go, so I approached the new guy that took over and explained the situation to him. I asked him if he would support me by escalating my request to extend their contract up to our CRO. 

Before promising that he would, he asked me if that’s what I wanted to do. I didn’t hesitate to say yes. 

I was a little bit naive at that moment, but I also knew I was doing the right thing. 

My client’s contract was extended and they ended up saving money on the deal. 

The next quarter, they renewed at a higher price, their business booming after their retail clients pivoted to online stores. 

I never made any money off that deal because I was fired before my client renewed their contract. By extending their contract out another quarter, I failed to bring in a large deal to the company and missed my quota. 

It does seem inevitable that I was going to be let go. Maybe denying them the contract extension would have kept me above water for one more quota. But I realized I didn’t like the rules of the game I was playing. I didn’t feel good about closing deals that were bad for my clients. 

I’ve been thinking about this incident recently because I’ve been reflecting on my money mindset. There are a few different money scripts that I am looking at tackling, but one thing that has stayed true over the last couple years is that I never want to make money out of integrity. 

I’m at a place in my life where I can make decisions from an abundance mindset and I want to honor that. When I was working on the first deal in this piece, I was so afraid of losing my job if the deal went poorly or having to pay out of my own pocket if the company didn’t renew. 

The difference in a scarcity mindset and abundance mindset is easy to see in sales. 

Whenever I was struggling to hit my quota, I would be desperate to get any deal in. When I had my best quarter, I could easily say no to “bad” deals and ironically cared more about my clients welfare. 

What I learned in my last sales role when every deal I received was a dumpster fire was that the scarcity mindset wasn’t serving me or my clients. 

So many things were out of my control, but halfway through my time at the company, I decided to stop compromising my integrity to try and make deals happen.

I started to actively seek out new companies to sell to so that I could build a strong positive foundation for our relationship. I became more comfortable pointing out when our product wasn’t a good fit for a company. I focused on improving the experience of working with me. My solutions architects were put to work when I kept hosting free lunch and learns for my clients engineering teams. 

Things turned around for me, but it was too little too late. 

At the least though, I left my job with integrity.